US2994697A - New dyestuffs of the 1, 8-naphthalene dicarboxylic acid series - Google Patents
New dyestuffs of the 1, 8-naphthalene dicarboxylic acid series Download PDFInfo
- Publication number
- US2994697A US2994697A US728554A US72855458A US2994697A US 2994697 A US2994697 A US 2994697A US 728554 A US728554 A US 728554A US 72855458 A US72855458 A US 72855458A US 2994697 A US2994697 A US 2994697A
- Authority
- US
- United States
- Prior art keywords
- parts
- dicarboxylic acid
- naphthalene dicarboxylic
- fastness
- acid series
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical class C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 title description 6
- 239000000975 dye Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 125000002843 carboxylic acid group Chemical group 0.000 description 8
- 238000004043 dyeing Methods 0.000 description 8
- 239000000835 fiber Substances 0.000 description 7
- 238000009998 heat setting Methods 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 5
- -1 polyethylene terephthalates Polymers 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- HEMGYNNCNNODNX-UHFFFAOYSA-N 3,4-diaminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1N HEMGYNNCNNODNX-UHFFFAOYSA-N 0.000 description 3
- KLLREYQZEOLXHA-UHFFFAOYSA-N 4-ethoxybenzene-1,2-diamine Chemical compound CCOC1=CC=C(N)C(N)=C1 KLLREYQZEOLXHA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010409 ironing Methods 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- WDVCRGRJQBYMAF-UHFFFAOYSA-N (3-hydroxynaphthalene-1-carbonyl) 3-hydroxynaphthalene-1-carboxylate Chemical compound C1=CC=CC2=CC(O)=CC(C(=O)OC(=O)C=3C4=CC=CC=C4C=C(O)C=3)=C21 WDVCRGRJQBYMAF-UHFFFAOYSA-N 0.000 description 1
- YUFBLWYGGOUMMA-UHFFFAOYSA-N 2-(2-hydroxy-2-phenylethoxy)-1-phenylethanol Chemical compound C=1C=CC=CC=1C(O)COCC(O)C1=CC=CC=C1 YUFBLWYGGOUMMA-UHFFFAOYSA-N 0.000 description 1
- OCISOSJGBCQHHN-UHFFFAOYSA-N 3-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC(O)=CC2=C1 OCISOSJGBCQHHN-UHFFFAOYSA-N 0.000 description 1
- WIHHVKUARKTSBU-UHFFFAOYSA-N 4-bromobenzene-1,2-diamine Chemical compound NC1=CC=C(Br)C=C1N WIHHVKUARKTSBU-UHFFFAOYSA-N 0.000 description 1
- 108091023288 HOTAIR Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- DDHQTWZKAJOZQL-UHFFFAOYSA-N naphthalene-1,4,5-tricarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O DDHQTWZKAJOZQL-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 239000001040 synthetic pigment Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/12—Perinones, i.e. naphthoylene-aryl-imidazoles
Definitions
- the present invention relates to new dyestufis of the 1,8-naphthalene dicarboxylic acid series and to a process for preparing them; more particularly it relates to dyestuffs corresponding to the following formula wherein the benzene nucleus may be substituted by a halogen atom, an alkyl, alkoxy, hydroxyl or carboxylic acid group or by the group OCH;C H OH and the naphthalene nucleus may be substituted by a hydroxyl or carboxylic acid group, and wherein at least one of the two nuclei contains at least one free hydroxyl or carboxylic acid group.
- the dyestuffs disclosed in the examples of this patent contain a chlorine atom, a methyl or methoxy group as substituent in the benzene nucleus of the ortho-diamine.
- dyestuffs possessing an excellent fastness to thermofixation and very good general fastness properties are obtained by condensing a 1,8- naphthalene dicarboxylic acid or its anhydride with an aromatic ortho-diamine in such a manner that the dyestufl formed contains at least one free hydroxyl or carboxylic acid group.
- the hydroxyl or carboxylic acid group can be introduced into the dyestuif molecule by condensing a l,8-naphthalene dicarboxylic acid with an aromatic ortho-diamine which contains a hydroxyl or carboxylic acid group in the benzene nucleus or a hydroxyl group in a side chain.
- the dyestuffs can be prepared in boiling organic sol- 2,994,697 Patepted Aug. 1, 1961 vents, such as pyridine, glacial acetic acid, chlorobenzene or ortho-dichlorobenzeneor even in water under pressure.
- the dyeings can be produced from an aqueous bath with the addition of a carrier, for example ortho-pheuylphenol or others, at a temperature near the boiling point or advantageously without the addition of a carrier at a temperature above C. under pressure.
- the dyestuffs are also very suitable for printing fabrics of polyesters.
- Example I A mixture of 19.8 parts of naphthalic acid anhydride, 16.5 parts of 3,4-diaminobenzene-1-carboxylic acid and parts of glacial acetic acid is heated at the boil for 3 hours.
- the dyestufi which crystallizes out on is filtered ofi with suction, washed with methanol and dried. It dyes polyester fibers from an aqueous dispersion greenish yellow tints of an excellent fastness to thermofixation.
- Example 2 19.8 parts of naphthalic acid anhydride are heated at the boil for several hours with 19 parts of 3,4-diamino phenyl-beta-hydroxyethylether in 300 parts of chlorobenzene.
- the dyestuti which precipitates from the solution can be used for dyeing and printing fabrics of polyesters brilliant greenish yellow tints.
- the dyestulf obtainable from naphthalic acid anhydride and 3,4-diamino-l-ethoxybenzene it is distinguished by its excellent fastness to thermofixation and to ironing.
- Example 3 21.4 parts of 3-hydroxynaphthalic acid anhydride are heated at the boil for 2 hours with 16 parts of 3,4-diaminobenzene-l-carboxylic acid in 200 parts of glacial acetic acid. When the solution is cooled, well formed yellow leaflets precipitate which can be recrystallized from a mixture of dimethylformamide and water. Polyester fibers are dyed from an aqueous dispersion greenish yellow tints of very good properties of fastness.
- Example 4 When 16 parts of 3,4-diamino-1-ch1orobenzene are used instead of 3,4-diaminobenzene-l-carboxylic acid indicated in Example 3, a dyestuff is obtained which dyes polyester fibers greenish yellow tints of an excellent fastness to thermofixation.
- Example 5 21.4 parts of B-hydmxynaphthalic acid anhydride and 17 parts of 3,4-diaminophenyl-beta-hydroxyethylether are heated at the boil for 2 hours in 200 parts of glacial acetic acid. The mixture is worked up and a crystalline greenish yellow dyestufi is obtained which is very suitable for dyeing and printing fabrics of polyesters on account of its very good properties of fastness,
- Example 6 When in Example 5 3,4-diamino-l-ethoxybenzene is used instead of 3,4-diaminophenyl-beta-hydroxyethylether, there is likewise obtained a greenish yellow dyestufi which has the same very good properties of fastness.
- Example 7 10 parts of naphthalene-1,4,5-tricarboxylie acid anhydride are heated at the boil for some hours with parts of ortho-phenyleuediamine'in 50 parts of pyridine. After cooling, the dyestufl formed is precipitated from the brown solution by-means of dilute hydrochloric acid. It can be purified by dissolving it in dilute caustic soda solution and reprecipitating it with a mineral acid after the solution has been clarified. Polyester fibers are dyed from an aqueous dispersion greenish yellow tints of very good properties of fastness. 1
- Example 8 30 parts of naphthalene-1,4,5-tricarboxylic acid are heated in an autoclave at 150-160 C. for 5 hours with 23 parts of 3,4-diaminophenyl-beta-hydroxyethylether in 300parts of water.
- the dyestulf which can readily be isolated after cooling yields on polyethylene glycol terephthalate fibers yellow dyeings of an excellent fastness to thermofixation.
- the dyestufi corresponding to the following formula 4 2.
- the dyestufi corresponding to the following formula o-cm-cn. 2o I References Cited in the file of this patent UNITED STATES PATENTS 2,820,037 Schmidt-Nickels Ian. 14, 1956; FOREIGN PATENTS 1,111,620 France Mar. 2, 1956; OTHER REFERENCES l Lubs. Chem. of Synthetic Dyes and Pigments, Rein f hold, N.Y., 1955, pp. 670 and 671. Schroeder et al.: Textile Research Journal, vol. xxxvn, No. 4, April 1951, pages 275-281.
Description
United States Patent 2,994,697 NEW DY'ESTUFFS OF THE 1,8-NAPHTHALENE DICA-RBOXYLIC ACID SERIES Wilhelm Eckert, Frankfurt am Main, Otto Fuchs, Hofheim (Taunus), and Friedrich Raizner and Heinz Rentel, am Main, Germany, assignors to Farbwerke Hoechst Alrtiengesellschaft vormals Meister Lucius & Briining, Frankfurt am Main, Germany, a corporation of Germany No Drawing. Filed Apr. 15, 1958, Ser. No. 728,554 Claims priority, application Germany Apr. 20, 1957 3 Claims. (Cl. 260-282) The present invention relates to new dyestufis of the 1,8-naphthalene dicarboxylic acid series and to a process for preparing them; more particularly it relates to dyestuffs corresponding to the following formula wherein the benzene nucleus may be substituted by a halogen atom, an alkyl, alkoxy, hydroxyl or carboxylic acid group or by the group OCH;C H OH and the naphthalene nucleus may be substituted by a hydroxyl or carboxylic acid group, and wherein at least one of the two nuclei contains at least one free hydroxyl or carboxylic acid group.
In .French a ent NQ- 20 is d c be 8 M99 for dyeing synthet fib s. in r s i p ye ter fib s. with condensation products of 1,8-naphthalene dicarboxylic acid or its anhydride and unsubstituted or substituted aromatic ortho-diamines. The dyestuffs disclosed in the examples of this patent contain a chlorine atom, a methyl or methoxy group as substituent in the benzene nucleus of the ortho-diamine.
Reworking of these examples revealed that the dyestufis described have a good atlinity for polyester fibers and that the dyeing produced possess a good fastness to wet processing and to ironing, but their resistance to hotair fixation (fastness to thermofixation) is only moderate. On account of this deficiency the dyestuffs are not suitable for use on a broader scale in the textile industry since in practice most of the dyeings are subjected to a hot-air fixation.
Now we have found that dyestuffs possessing an excellent fastness to thermofixation and very good general fastness properties are obtained by condensing a 1,8- naphthalene dicarboxylic acid or its anhydride with an aromatic ortho-diamine in such a manner that the dyestufl formed contains at least one free hydroxyl or carboxylic acid group. The hydroxyl or carboxylic acid group can be introduced into the dyestuif molecule by condensing a l,8-naphthalene dicarboxylic acid with an aromatic ortho-diamine which contains a hydroxyl or carboxylic acid group in the benzene nucleus or a hydroxyl group in a side chain. It is also possible to condense 1,8-naphthalene dicarboxylic acid substituted in the naphthalene nucleus by a hydroxyl or carboxylic acid group, with a substituted or unsubstituted aromatic ortho-diamine. It is essential that at least one free hydroxyl or carboxylic acid group is present in the dyestutl molecule.
The dyestuffs can be prepared in boiling organic sol- 2,994,697 Patepted Aug. 1, 1961 vents, such as pyridine, glacial acetic acid, chlorobenzene or ortho-dichlorobenzeneor even in water under pressure. The new dyestufls ,dye fibers and foils of aromatic polyesters, especially polyethylene terephthalates, greenish yellow to golden orange tints which are distinguished by very good properties of fastness, especially by an excellent fastness to thermofixation. The dyeings can be produced from an aqueous bath with the addition of a carrier, for example ortho-pheuylphenol or others, at a temperature near the boiling point or advantageously without the addition of a carrier at a temperature above C. under pressure. The dyestuffs are also very suitable for printing fabrics of polyesters.
The following examples serve to illustrate the inven' tion but they are not intended to limit it thereto, the parts being by weight:
Example I A mixture of 19.8 parts of naphthalic acid anhydride, 16.5 parts of 3,4-diaminobenzene-1-carboxylic acid and parts of glacial acetic acid is heated at the boil for 3 hours. The dyestufi which crystallizes out on is filtered ofi with suction, washed with methanol and dried. It dyes polyester fibers from an aqueous dispersion greenish yellow tints of an excellent fastness to thermofixation.
Example 2 19.8 parts of naphthalic acid anhydride are heated at the boil for several hours with 19 parts of 3,4-diamino phenyl-beta-hydroxyethylether in 300 parts of chlorobenzene. The dyestuti which precipitates from the solution can be used for dyeing and printing fabrics of polyesters brilliant greenish yellow tints. As compared with the dyestulf obtainable from naphthalic acid anhydride and 3,4-diamino-l-ethoxybenzene it is distinguished by its excellent fastness to thermofixation and to ironing.
Example 3 21.4 parts of 3-hydroxynaphthalic acid anhydride are heated at the boil for 2 hours with 16 parts of 3,4-diaminobenzene-l-carboxylic acid in 200 parts of glacial acetic acid. When the solution is cooled, well formed yellow leaflets precipitate which can be recrystallized from a mixture of dimethylformamide and water. Polyester fibers are dyed from an aqueous dispersion greenish yellow tints of very good properties of fastness.
Example 4 When 16 parts of 3,4-diamino-1-ch1orobenzene are used instead of 3,4-diaminobenzene-l-carboxylic acid indicated in Example 3, a dyestuff is obtained which dyes polyester fibers greenish yellow tints of an excellent fastness to thermofixation.
When 3-hydroxynaphthalic acid is reacted with 3,4- diamino-l-bromobenzene under the conditions described in Example 3, there is likewise obtained a greenish yellow dyestuif of very good properties of fastness.
Example 5 21.4 parts of B-hydmxynaphthalic acid anhydride and 17 parts of 3,4-diaminophenyl-beta-hydroxyethylether are heated at the boil for 2 hours in 200 parts of glacial acetic acid. The mixture is worked up and a crystalline greenish yellow dyestufi is obtained which is very suitable for dyeing and printing fabrics of polyesters on account of its very good properties of fastness,
Example 6 When in Example 5 3,4-diamino-l-ethoxybenzene is used instead of 3,4-diaminophenyl-beta-hydroxyethylether, there is likewise obtained a greenish yellow dyestufi which has the same very good properties of fastness.
Example 7 10 parts of naphthalene-1,4,5-tricarboxylie acid anhydride are heated at the boil for some hours with parts of ortho-phenyleuediamine'in 50 parts of pyridine. After cooling, the dyestufl formed is precipitated from the brown solution by-means of dilute hydrochloric acid. It can be purified by dissolving it in dilute caustic soda solution and reprecipitating it with a mineral acid after the solution has been clarified. Polyester fibers are dyed from an aqueous dispersion greenish yellow tints of very good properties of fastness. 1
Example 8 30 parts of naphthalene-1,4,5-tricarboxylic acid are heated in an autoclave at 150-160 C. for 5 hours with 23 parts of 3,4-diaminophenyl-beta-hydroxyethylether in 300parts of water. The dyestulf which can readily be isolated after cooling yields on polyethylene glycol terephthalate fibers yellow dyeings of an excellent fastness to thermofixation.
When 21 parts of 3,4-diamino1-ethoxybenzene are used instead of 3,4-diaminophenyl-beta-hydroxyethyl ether, a beautiful golden yellow dyeing of the same fastness properties is obtained. With the use of 3,4-diaminol-methoxybcnzene a dyestulf is obtained which likewise yields golden-yellow tints.
We claim:
1. The dyestufi corresponding to the following formula 4 2. The dyestufl corresponding to the following formuls N 10 o= Y on I 7 3. The dyestufi corresponding to the following formula o-cm-cn. 2o I References Cited in the file of this patent UNITED STATES PATENTS 2,820,037 Schmidt-Nickels Ian. 14, 1956; FOREIGN PATENTS 1,111,620 France Mar. 2, 1956; OTHER REFERENCES l Lubs. Chem. of Synthetic Dyes and Pigments, Rein f hold, N.Y., 1955, pp. 670 and 671. Schroeder et al.: Textile Research Journal, vol. xxxvn, No. 4, April 1951, pages 275-281.
Claims (1)
1. THE DYESTUFF CORRESPONDING TO THE FOLLOWING FORMULA
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2994697X | 1957-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2994697A true US2994697A (en) | 1961-08-01 |
Family
ID=8083854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US728554A Expired - Lifetime US2994697A (en) | 1957-04-20 | 1958-04-15 | New dyestuffs of the 1, 8-naphthalene dicarboxylic acid series |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2994697A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3459489A (en) * | 1965-04-13 | 1969-08-05 | Ugine Kuhlmann | Cationic dyestuffs,mixtures thereof and their use in dyeing fibers based on acrylonitrile |
| WO1993023492A1 (en) | 1992-05-13 | 1993-11-25 | Molecular Probes, Inc. | Fluorescent microparticles with controllable enhanced stokes shift |
| US5723218A (en) * | 1990-04-16 | 1998-03-03 | Molecular Probes, Inc. | Dipyrrometheneboron difluoride labeled flourescent microparticles |
| EP1245645A2 (en) * | 2001-03-29 | 2002-10-02 | Bayer Ag | Crystal modification of a perinone dye |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1111620A (en) * | 1954-09-17 | 1956-03-02 | Cfmc | Process for coloring synthetic fibers and new industrial products resulting therefrom |
| US2820037A (en) * | 1956-05-24 | 1958-01-14 | Gen Aniline & Film Corp | Benzimidazobenzoisoquinolines |
-
1958
- 1958-04-15 US US728554A patent/US2994697A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1111620A (en) * | 1954-09-17 | 1956-03-02 | Cfmc | Process for coloring synthetic fibers and new industrial products resulting therefrom |
| US2820037A (en) * | 1956-05-24 | 1958-01-14 | Gen Aniline & Film Corp | Benzimidazobenzoisoquinolines |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3459489A (en) * | 1965-04-13 | 1969-08-05 | Ugine Kuhlmann | Cationic dyestuffs,mixtures thereof and their use in dyeing fibers based on acrylonitrile |
| US5723218A (en) * | 1990-04-16 | 1998-03-03 | Molecular Probes, Inc. | Dipyrrometheneboron difluoride labeled flourescent microparticles |
| WO1993023492A1 (en) | 1992-05-13 | 1993-11-25 | Molecular Probes, Inc. | Fluorescent microparticles with controllable enhanced stokes shift |
| US5326692A (en) * | 1992-05-13 | 1994-07-05 | Molecular Probes, Inc. | Fluorescent microparticles with controllable enhanced stokes shift |
| US5573909A (en) * | 1992-05-13 | 1996-11-12 | Molecular Probes, Inc. | Fluorescent labeling using microparticles with controllable stokes shift |
| EP1245645A2 (en) * | 2001-03-29 | 2002-10-02 | Bayer Ag | Crystal modification of a perinone dye |
| US20020193577A1 (en) * | 2001-03-29 | 2002-12-19 | Stephan Michaelis | Novel crystal form of a perinone dye |
| EP1245645A3 (en) * | 2001-03-29 | 2003-12-03 | Bayer Ag | Crystal modification of a perinone dye |
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